DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restriction
In a telephone call dated 08/13/2025, Applicant was required to select one metal, M, specify what type of ring the two substituents, RE are joined to form, and specify which ring of Formula II is coordinated to metal, M.
In this call, a species wherein M is iridium and wherein two RE are joined to form a 6-membered, aromatic ring which is further coordinated to the metal M was elected. This will be herein after referred to as Species I.
In the claims dated 11/19/2025, claim 28 was added, which is not encompassed by Species I.
Claims 6, 16, and 28 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
Species I, drawn to claims 1-2, 5, 8-9, 11-13, 17, and 20-27, is examined herein.
Response to Amendment
In the response filed 11/19/2025, the claims and specification were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims and specification, the objections to claim 19 and the specification are withdrawn by the Office.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claims 6 and 19 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, the rejection under 35 U.S.C. 112(d) of claim 19 as being of improper dependent form, and the rejection under 35 U.S.C. 102(a)(2) of claims 1-4, 8, and 11-13 as being anticipated by Kwon et al. (US 2022/0069237 A1) are withdrawn by the Office.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 101 of claims 1-5, 8, and 11-12 as claiming the same invention as copending Application No. 17/985,088, and the provisional non-statutory double patenting rejection of claims 9-10, 13-15, and 17-20 as being unpatentable over claims 9-10, 13-15, and 17-20 of copending Application No. 17/985,088 are withdrawn by the Office.
Claims 1, 6, 8, 9, 17, and 20 have been amended.
Claims 21-28 have been added.
Claims 3, 4, 7, 10, 14, 15, 18, and 19 have been canceled.
Claims 1-2, 5-6, 8-9, 11-13, 16-17, and 20-28 are pending in the application,
of which, claims 6, 16, and 28 are withdrawn.
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive. Applicant’s amendments do not overcome the prior art because the prior art still reads on the claimed invention.
A reinterpretation of the prior art is given below to explain how the prior art still reads on the claimed invention.
Claim Objections
Claims 1, 17, 20, and 27 are objected to because of the following informalities:
The letters, numbers, and bonds in the chemical structure given in Formula IIa are illegible. Please correct these structures so all letters, numbers, and bonds are clearly visible. See the example below.
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Applicant may wish to make this formula clearer by increasing font size, making the font bold, and/or making the lines thicker.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-2, 5, 8-9, 11-13, 17, and 20-27 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With respect to independent claims 1, 17, and 20, the claims contain an amendment with confusing formatting following the phrase, “wherein at least one of the following is true:”.
The uncertainty is caused by the fact that conditions (a) and (b) are followed by a comma, which is typically used to separate alternatives in lists of related limitations, but conditions (c) and (d) are both followed by a semicolon, which is typically used to denote the end of a specific limitation or group of alternative limitations. The letter sequence of (a), (b), (c), and (d) implies the limitations are alternatives, but the formatting implies that condition (d) is unrelated to conditions (a) through (c).
In continuing examination, the semicolon after (c) is being interpreted as a typographical error, and conditions (a) through (d) are being interpreted as a single set of limitations referred to in the alternative, wherein only one of conditions (a) through (d) must be true.
With respect to claim 8, the claim contains reference to canceled Formula IIb.
In continuing examination, this limitation will also be considered as canceled.
Claims 2, 5, 9, 11-13, and 21-27 are rejected by virtue of dependency.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-2, 5, 8-9, 11-13, 17, 20-23, 25, and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Kwon et al. (US 2022/0069237 A1).
With respect to claim 1, Kwon discloses compound 1 (paragraph 0145), which is pictured below.
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This compound is derived from Kwon Formula 1, comprising a ligand of Kwon Formula 1A (paragraph 0012), which is pictured below.
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Kwon also teaches that Y1 is carbon and Y2 is nitrogen (paragraph 0014).
Such a modification produces a compound that meets the requirements of condition (b) and proviso (1)(ii) of instant Formula I when T’ is N, moiety A is a monocyclic 6-membered carbocyclic ring (benzene), Z2 is nitrogen and Z1 is carbon, K1 and K2 are both a direct bond, and moiety B comprises a structure of Formula II. In formula II, X1-X7 are carbon atoms, T’ is a nitrogen atom, RA RC and RD are each hydrogen atoms and two RE are joined to form the pyridine ring of moiety B which is coordinated to metal, M, and M is iridium.
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select Z1 as carbon and Z2 as nitrogen from the finite number of possible combinations and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 2, Kwon teaches the compound of claim 1, and RA, RC, and RD are each hydrogen atoms and RE is coordinated to metal M, as discussed above.
With respect to claim 5, Kwon teaches the compound of claim 1, as discussed above.
In Formula IA, pictured and discussed above, Kwon also teaches that ring A1 is a C10 carbocyclic group (paragraph 0053), such as naphthyl (paragraph 0249, line 7).
Such a modification produces a compound that meets the requirements of the instant claim when two of RA are joined to form a ring fused to ring A.
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known carbocyclic group from each of the finite lists of possible carbocyclic groups to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 8, Kwon teaches the compound of claim 1, and the ligand LA has the structure of Formula IIa, wherein one of X8 through X11 is a nitrogen, and each remaining X character is carbon, as discussed above.
With respect to claim 9, Kwon teaches the compound of claim 8, as discussed above.
Kwon also teaches that R10, R30, and R40 may be a C1 alkyl (methyl) group (paragraph 0078 and 0079 line 6).
Such a modification produces a ligand LA which has the structure of LAII4-(X2)(X2)(R1)(R1)(R1)(R1).
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent, such as methyl, from the finite list of possible substituents to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claims 11 and 12, Kwon teaches the compound of claim 1, and the compound has the formula Ir(LA)(LB)2 wherein p is 1 and q is 2 and 3 is the oxidation state of iridium, as pictured above.
With respect to claim 13, Kwon teaches the compound of claim 11, and LB has the formula below which is the sixth embodiment of the instant claim. LC is not present.
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With respect to claim 17, Kwon teaches an organic light emitting device comprising an anode, a cathode (paragraph 0160), and an organic layer (paragraph 0164) and the organic layer comprises compound 1 (paragraph 0145), which is pictured below.
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This compound is derived from Kwon Formula 1, comprising a ligand of Kwon Formula 1A (paragraph 0012), which is pictured below.
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Kwon also teaches that Y1 is carbon and Y2 is nitrogen (paragraph 0014).
Such a modification produces a compound that meets the requirements of condition (b) and proviso (1)(ii) of instant Formula I when T’ is N, moiety A is a monocyclic 6-membered carbocyclic ring (benzene), Z2 is nitrogen and Z1 is carbon, K1 and K2 are both a direct bond, and moiety B comprises a structure of Formula II. In formula II, X1-X7 are carbon atoms, T’ is a nitrogen atom, RA RC and RD are each hydrogen atoms and two RE are joined to form the pyridine ring of moiety B which is coordinated to metal, M, and M is iridium.
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select Z1 as carbon and Z2 as nitrogen from the finite number of possible combinations and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to include the compound in the organic layer of a device with the claimed device structure, as taught by Kwon.
With respect to 20, Kwon teaches a consumer product such as a full-color organic light emitting device (paragraph 0218) comprising an organic light emitting device, comprising an anode, a cathode (paragraph 0160), and an organic layer (paragraph 0164) and the organic layer comprises compound 1 (paragraph 0145), which is pictured below.
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This compound is derived from Kwon Formula 1, comprising a ligand of Kwon Formula 1A (paragraph 0012), which is pictured below.
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Kwon also teaches that Y1 is carbon and Y2 is nitrogen (paragraph 0014).
Such a modification produces a compound that meets the requirements of condition (b) and proviso (1)(ii) of instant Formula I when T’ is N, moiety A is a monocyclic 6-membered carbocyclic ring (benzene), Z2 is nitrogen and Z1 is carbon, K1 and K2 are both a direct bond, and moiety B comprises a structure of Formula II. In formula II, X1-X7 are carbon atoms, T’ is a nitrogen atom, RA RC and RD are each hydrogen atoms and two RE are joined to form the pyridine ring of moiety B which is coordinated to metal, M, and M is iridium.
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select Z1 as carbon and Z2 as nitrogen from the finite number of possible combinations and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Further, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to include the compound in the organic layer of a consumer device comprising an organic light emitting device with the claimed device structure, as taught by Kwon.
With respect to claim 21, Kwon teaches the compound of claim 8, as discussed above.
The formula of Kwon comprises variable bond locations as pictured above. In this respect, the modification discussed above can be used to arrive at more than one compound of the instant claim, such as the third and eleventh embodiments, which are pictured below.
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Kwon includes each bonding pattern claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned bonding pattern being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any claimed bonding pattern from the finite number of possible bonding combinations and arrive at a compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 22, Kwon teaches the compound of claim 12, as discussed above.
Kwon also teaches that R10, R30, and R40 may be a C1 alkyl (methyl) group (paragraph 0078 and 0079 line 6).
Such a modification produces a ligand LA which has the structure of LAII4-(X2)(X2)(R1)(R1)(R1)(R1)(LB1)2.
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent, such as methyl, from the finite list of possible substituents to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 23, Kwon teaches the compound of claim 12, as discussed above.
Kwon also teaches that ring A2 is a C4 heterocyclic group (paragraph 0013), and examples of heterocycles include pyrimidine (paragraph 0250, line 10).
Such a modification produces a compound the first compound on page 57 of the claims.
Kwon includes each element claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select Z1 as carbon and Z2 as the nitrogen atom of a pyrimidine group from the finite number of possible combinations and arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claim 25, Kwon teaches the compound of claim 1, and Z2 is nitrogen, as discussed above.
With respect to claim 27, Kwon teaches the compound of claim 1, as discussed above.
Formula 1A of Kwon comprises variable bonding of L1, L2, and the amine nitrogen to ring A2. In this respect, Formula 1A can be used to arrive at any one of the listed bonding patterns.
Kwon includes each bonding pattern claimed, with the only difference between the claimed invention and Kwon being a lack of the aforementioned bonding pattern being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any claimed bonding pattern from the finite number of possible bonding combinations and arrive at a compound of the instant claim since the combination of elements would have yielded the predictable result of an organometallic compound which, when used in an organic electronic device, such as an organic light-emitting device, results in low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon (paragraph 0146), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
Claim 26 is rejected under 35 U.S.C. 103 as being unpatentable over Kwon et al. (US 2022/0069237 A1) as applied above and further in view of Yi et al. (US 2021/0288268 A1).
With respect to claim 26, Kwon teaches the compound of claim 1, as discussed above.
However, Kwon does not teach that a position analogous to instant K1 or K2 is not a direct bond.
In analogous art, Yi teaches an iridium (paragraph 0052) organometallic compound for use in an organic light-emitting device (abstract).
Yi teaches that the iridium compound of Formula 1 (paragraph 0007) comprises at least one ligand represented by Formula 2A or Formula 2B (paragraph 0010), which are pictured below.
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In these formulae, Y1 may be an oxygen atom, sulfur atom, or substituted nitrogen atom (paragraph 0016) and * and *’ each indicate a binding site to M in Formula 1 (paragraph 0028).
Yi teaches that since ring CY21 of Formula 2A and 2B is linked to metal M of Formula 1 via Y1, a cyclometalated ring formed by metal M and ligand L1 of Formula 1 may be a 6-membered ring. Thus, hole transport characteristics of the organometallic compound represented by Formula 1 may be enhanced.
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to incorporate an oxygen, sulfur, or substituted nitrogen linking group between the iridium nucleus and ligand in the compound of Kwon in order to form a 6-membered ring, and enhance the hole transport characteristics of the compound, as taught by Yi.
Conclusion
Applicant's amendment necessitated any new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RACHEL SIMBANA/Examiner, Art Unit 1786